Five Spots to Eat, Drink and Be Merry Outdoors This Summer

Includes a new rooftop bar. And yes, that’s a pool.

By Maggie Hennessy

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25 May 2017

This is just one installment of 37 Things a Man's Gotta Do This Summer, our annual compendium of everything worth seeing, doing, eating, drinking and generally making time for in your neck of the woods between now and September.

Next question: Where? Find those answers here, in our roundup of Chicago’s best new outdoor dining venues.

A rooftop with a pool. Brewskis with a pooch. The backyard to end all backyards.

Dine on and drink well, fellas.

For a Backyard Party: Lawrence House FlatsBecause we all need the occasional break from urbanity, but can’t always get away, the massive new backyard at the beautifully renovated Lawrence House Flats awaits. What to expect when the patio opens some time this June: seating for up to 100, broken into three sections. You've got plush loungers for two in the grass, a twinklelight-draped patio with tables and chairs and a huge stone fire pit surrounded by adirondack chairs. The masterful barmen at Uptown’s best tippling den Larry’s will keep you satiated with seasonal drinks. If that still doesn’t grab you, there’ll be movie nights, live music and rotating food pop-ups all summer long. How about it?

For Drinking Among Swimsuits: The Cabana ClubNew to Wicker Park’s outdoor dining options this year: a rooftop. With a pool. Yep, ya heard right. And it’s all thanks to The Robey’s sexy new indoor/outdoor rooftop bar. With 180-degree views extending down Milwaukee Ave. to downtown, there are vacation vibes aplenty here. Margaritas help. But don’t plan on dipping in that triangular pool unless you’re a guest at the hotel. If you’re looking for more of a South Beach after-2 a.m. atmosphere, come back most Saturday nights, when the whole place transforms into a DJ-powered pool party, complete with buckets of Corona and rosé all night.

For Beer and Vaudeville Antics: Tour de FatBack at it for god knows how long, this eccentric New Belgium-sponsored bike, beer and music fest is moving to Northerly Island to accommodate even more revelers and one larger-than-life headlining musical act. Because if anything can top ice-cold brews, vaudeville acts, magicians, comedians and mind-blowing provocateurs, it would be hip-hop legends the Roots. July 29th ain’t far away, so grab those tickets. Proceeds benefit West Town Bikes. Costumes and antics encouraged.

For Bringing Man’s Best Friend: Broken English IICold brewskis and tacos all but scream summertime in our fair city. Even better when the doggo can come along. You’ll have 60 seats (10 up front, 50 in back) to pick from outside the bustling Lincoln Park outpost of taco joint Broken English. We’d suggest heading straight for the sprawling, greenery-enclosed back patio, overseen by graffiti master JC Rivera’s always-melancholy Bear Champ. There’s even a walk-up bar so you don’t have to leave the pooch unattended to grab the next round.

For the Best Rooftop Makeover: ApogeeOut with the old, in with the absolutely outrageous. That’s what you’ll get at Apogee — the new destination-worthy indoor/outdoor cocktail spot that replaced the Vertigo Lounge on the 26th floor of the Dana Hotel. Several cocktails are designed for sharing, so bring the whole crew to sample barman/mad scientist Benjamin Schiller’s (The Sixth, The Berkshire Room) handiwork. Fancy a Mr. Nice Guy (vodka, white sage and pineapple) from a blackberry smoke-filled bong? Check. Or a tiki drink in a real coconut? Done. Try to snag a spot on the 1,100 sq.-ft. outdoor patio, where the only thing that hasn’t changed is the killer views.